


Rouge's Brothel: Bondage Night

by The_Cyborg_Fox



Series: Tails and the girls of Mobius [21]
Category: Sonic the Hedgehog - All Media Types
Genre: Bondage, Breast Fucking, Brothels, Cock Rings, Cock Tease, Go Read 'Rouge's Brothel' on Fanfiction.Net for more information, Hand Jobs, Handcuffs, I don't Actually Support It in Real Life, Incest, It's just for the fic, Large Breasts, Large Cock, Mommy Kink, Multi, Other Additional Tags to Be Added, Other Ships Not Mentioned in Tags, Parent/Child Incest, Pastiche of Another fic from Fanfiction.Net, Please don't Hate me for Incest, Rope Bondage, Teasing, Threesome - F/F/M, sexy outfits
Language: English
Status: Completed
Published: 2020-12-13
Updated: 2021-02-09
Packaged: 2021-03-10 03:08:59
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 19,969
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27947318
Author URL: https://archiveofourown.org/users/The_Cyborg_Fox/pseuds/The_Cyborg_Fox
Summary: Requested by SuperSonicBros123 and yep, it's another tribute to another fic, being Rouge's Brothel by rdphoenix07. Tails learns that it is Bondage Night at Rouge's Brothel, where every customer is to be dommed and served by two of the girls working there. Remembering that one time with Fiona, Tails decides to go over and try it again by himself as Sonic, Knux and Shadow are busy. What sort of fun bondage will await him tonight?
Relationships: Blaze the Cat/Miles "Tails" Prower, Fiona Fox/Miles "Tails" Prower, Miles "Tails" Prower/Rouge the Bat, Miles "Tails" Prower/Vanilla the Rabbit, Miles “Tails” Prower/Rosemary Prower, Mina Mongoose/Miles "Tails" Prower
Series: Tails and the girls of Mobius [21]
Series URL: https://archiveofourown.org/series/1847656
Comments: 11
Kudos: 3





	1. Blaze and Mina

**Author's Note:**

> So just like with my 'Tails the God' fic, the original idea of this work comes from the user rdphoenix07. He is the original creator of 'Rouge's Brothel'. If you like these sorta smut fics, I would recommend reading all of his Rouge's Brothel fics, and even some of his other fics. Also, this fic has no actual canon resemblance to Rouge's Brothel, Casino Nights, Rouge's Brothel: Beginnings, or Rouge's Brothel: Reconcile. This is a non-canon request fic from SuperSonicBros123, that I got permission from rdphoenix07 to write. Just a reminder, I don't want people saying that I 'stole' this idea. The only thing about the 'Rouge's Brothel' series I technically own is this short 3 chapter fic.
> 
> But enough about that, onto the fic itself. Just note that I am taking a short break from 'Tails's Harem Tale', and this will be the focus until all three chapters are done, so a poll will be posted on my profile for you guys to decide what you want to see next, and I would appreciate it if you go vote on it. Also unlike 'Tails the God' I might do more requests for this series if rdphoenix07 lets me, but even if he does, that's still a big 'might'. But anyways, I hope you enjoy this fic cos: here we go.

Miles 'Tails' Prower stood in front of the building before him. It was an old fashioned building that still seemed to be in good shape. But he had been here before, and he had enjoyed his night. It was a brothel, owned by a beautiful bat named Rouge. Normally he would be a bit nervous standing in front of a place like this, but ever since he had spent his first night here, he had grown plenty of confidence. He had met many girls that night and he had a lot of fun with them.

Why was he back? Well, what was wrong with coming a second time? Actually this was not his second time coming back, but he had heard from an outsider that Rouge was hosting something special tonight. It was a little something that she would call 'Bondage Night'. From what he had heard so far, all customers were to be tied down and dominated by two girls.

One would not assume that Tails was the type of person who would be into that. But the night after Tails spent his first night in the brothel he had met a red vixen named Fiona. Fiona was not exactly the nicest girl he had met in this building, and she did twist his arm and tie him down to her bed without her even giving him a small warning. But despite the vixen's rough attitude, he did actually enjoy his time with her. Heck, he had even turned the tables against her and managed to escape her grasp and tie her down so that he could have his own turn with her.

Though Tails imagined that he wouldn't be given that chance again tonight, because he would be dommed by two girls not one. Plus, he didn't know every single girl in the building. He had met all them at least once but he had only 'spent time' with seven of them, including the owner herself. There were twenty four girls in total working here, and he assumed that Rouge would still be willing to hire some more for more variety. But the point was that he had only had fun with seven girls, if he were to go through with this with a new girl he had no idea what they'd be like. Well, there was only one way to find out.

Walking through the iron gate, up to the entrance, Tails walked into the more modernised part of the building. He walked into a slightly dimmed room with a front desk, and waiting for him was none other than the owner, Rouge. The bat was dressed in her usual tight corset which did not do much to hide her large breasts.

"Well, well, well" she said in her usual sultry tone upon recognising the two tailed fox immediately "It's a pleasure to see you again little fox."

"Hey Rouge" he said, smiling politely at her.

"It seems as though you've heard about what's going on here tonight" she said, giving a soft laugh.

"Yeah" said Tails, rubbing the back of his head "When I heard about it, the first thing I thought of was that one time I spent with Fiona."

"So you've come to experience it again, hmm?" she said, smiling widely.

"Yes" said Tails.

"Well, I hope you enjoy yourself" said Rouge "Believe it or not but it was actually her idea. Well, her idea and Lien-Da's. Bondage is kind of their thing. By the way, may I ask where are the other three?"

"Oh yeah" said Tails "I told Sonic, Knux and Shadow about this. They were interested for sure, but they were too busy to come tonight. So it's just me."

"Hmm, that's a shame" said Rouge "I would've liked to have seen them again. But that's okay, maybe I can host a night like this again so that they can experience it too. But I do admire how a young fox like you has decided to be bold enough to come here all by himself."

"Heh, thanks" said Tails.

"Well, since you are a regular here at the brothel, you get special services from me and my girls" said Rouge.

"Really? What kind of services?" asked Tails, interested.

"Well, you may be with not one, but three pairs of girls" said Rouge.

"Wow" said Tails, zoning out at the thought of being tied down and dominated by three pairs of girls.

"Well, what are you waiting for?" said Rouge "Come in and go enjoy yourself."

Tails nodded and walked into the main area. He wondered who to start with. He already knew there were plenty of choices. He figured he might was well go and try and spend some time with someone new at least once tonight. He looked around and he quickly found someone who had caught his eye. Walking around, there was a female mongoose. She had yellow fur and purple hair, she wore a black tank top and blue shorts. Tails often heard Sonic talk about this girl, he himself had only met her a couple times, but he was well aware of this girls beautiful singing voice. This mongoose went by the name of Mina. She has made quite a name for herself here at the brothel.

Noticing her made Tails wonder just how much fun she was as Sonic said she was. Wanting to find out, he quickly caught up to her. Upon hearing his voice, Mina turned around and came face to face with the young fox.

"Oh, well hello" she said, smiling sweetly at him.

'Wow her voice really is beautiful' thought Tails 'Makes me wonder how much more beautiful it is when she sings.'

"Yeah, hi Mina" said the fox "I don't know if you remember, but I'm one of Sonic and Knuckle's friends, Tails."

"How could I forget a cute fox like yourself?" giggled the mongoose "I know we haven't spent a lot of time together, but Sonic's already told me tons about you."

"Heh, cool" said Tails, realising that Mina was bending over slightly, giving him a look at her breasts which were barely covered by her tank top.

"So I feel like your hear for a specific reason?" said Mina.

"Oh yeah" said Tails "I feel like I don't have to explain why I'm here. Rouge already told me what's going down here tonight."

"Well, were you looking to be tied down and dommed by me?" asked Mina, using her hand to tug down her shirt slightly, showing off hints of a nipple.

"Yes" Tails said, almost robotically, making the mongoose giggle slightly.

"Well, give me a second" said Mina "The rule is that our customers are dommed by two girls, not just one. I think I've got someone in mind to join us."

Tails watched her leave and sat down and waited for Mina to return. As he waited he noticed a familiar red vixen dressed in a black tank top and tight black pants, walking down to the entrance of the VIP lounge. Said vixen turned around and recognised him immediately. Smiling mischievously the red fox walked over to him and stared down at him. He too recognised her as she got closer. It was Fiona, the one reason why he thought he would give the theme of tonight a try.

"Well look who it is" she said to him as she got close.

"Hello Fiona" said Tails, smiling at her.

"I had a feeling you would show up tonight" she said to him "Have you gotten the chance to get absolutely fucked by two girls?"

"Not yet, but I'm getting there" said Tails "I'm waiting for Mina, she said she had someone in mind to join us."

"Shame, your already taken" Fiona sighed, slightly disappointed "Well if your going to be occupied at the moment, you wouldn't mind doing me a favour after your finished. Come see me, and I'll show you some more fun."

"I promise" said Tails nodding.

Fiona gave Tails a seductive wink and left him, walking off into the VIP area. Tails watched her go, he noticed that she was swinging her tail from left to right teasingly.

"Tails" came Mina's sweet voice again. Tails turned and there was said mongoose walking over to him, and she was not alone. With her was a sexy purple female cat, who was dressed in some white shorts and tank top, her hair was tied up with a red scrunchie. She looked to already be slightly tired, but not from sex.

"I assume you've also been told about my friend Blaze" said Mina.

"Hello Tails" said the cat, smiling warmly at the fox "I've just finished some intense exercise. If you didn't know, I like to keep in shape."

"I can tell" said Tails, standing up.

"So, now that we've got Blaze with us, are you ready to have some fun Tails?" asked Mina.

"I sure am" said the fox, enthusiasm all over his voice "Where are we going?"

"Follow me" said Blaze, motioning both of them with her hand "We'll take thus to my room."

Tails and Mina followed Blaze back into the VIP lounge, which is where Blaze's room was. Rouge had set up Blaze's room to be right next to the gym she liked to train in. In a coincidence just as Tails, Mina and Blaze had left the room, another fox had entered the building. She was dressed in a blue dress and had beautiful brown fur. If Tails had stayed for a bit longer he would've recognised this woman, it was his mother Rosemary.

"So this is the place" she said to herself, looking around "Now I wonder if I can get a quick conversation with the owner."

Fiona strode up to Rouge's office and was greeted by two security guards. She had it in her mind mind to have a quick chat to the brothel owner.

"Evenin' Fiona" said one of the guards "We assume you want to talk to Rouge."

"You catch on quick" said Fiona.

"Well go right on in" said the other guard.

Fiona walked right past them through the office door, welcomed by Rouge who was sitting at her desk. Looking up, Rouge smiled as Fiona walked over to her and sat down on the chair in front of her desk.

"Hello Fiona" said Rouge "Come to get your thank you?"

"You catch on quick, like the security guards" said Fiona, smiling widely at the bat.

"Guess we have something in common" laughed Rouge "But really, I do owe you and Lien-Da for this idea. I'll admit, I was slightly sceptical about this. I mean, I've done bondage before, but I didn't think it was something a lot of our customers would be too keen on. But I have to say, business is still as good as ever.

"Well there's nothing else for me to say but, your welcome" said Fiona.

"Did you also happen to see who took particular interest in tonight's theme?" Rouge asked her.

"Oh yes" said Fiona, her grin widening "I just met him actually."

"I am kind of sad that the other three couldn't make it" said Rouge "But I guess one is better than none right?"

"Definitely not" said Fiona, leaning forward onto the desk "Say, would you like to tag team him after he's finished with Mina and Blaze?"

"Hm, I think I can squeeze that into my schedule" said Rouge, mirroring Fiona's grin.

As they planned out how they would do this there was a sudden knock at the door. Fiona quickly hopped out of her seat and walked over to the office door, opening it she was greeted with one of the guards.

"Hello? Yes, there is a woman who would like to speak with you Rouge" said the guard.

"Oh? Well, show her in" said an interested Rouge.

The guard moved away from the door and Fiona stepped aside to let in a brown fox dressed in a blue dress. Rouge looked her over, she had to say, this fox was quite the looker, if she had come to get a job here she could definitely arrange that.

"Fiona, could you get an extra chair for our guest?" she asked the vixen.

Fiona found a spare chair laying around and seated it in front of her desk, she then motioned for the fox lady to sit down. The brown fox took a seat and placed her hands neatly in her lap, Fiona sitting next to her in her chair.

"I assume you are the owner of this brothel" said the fox lady.

"Got it in one" said Rouge "And who am I speaking to?"

"My name is Rosemary, and I've come to have a temporary job here tonight" said the fox.

"Temporary?" said Fiona, staring at the fox questionably "If you only insist on working here for one night, why don't you just go out and find some random John for a one night stand."

"Well, I heard what kind of night was going on tonight" said Rosemary "And... Oh this is so hard for me to talk about."

"Let it out dear" said Rouge "What is it?"

"Well... I am Tails's mother" said Rosemary "And I have knowledge that he is visiting this place."

Rouge and Fiona stared at the older fox in amazement. While they were surprised, the could certainly see a resemblance between the two. What was Tails's mother doing here?

"Here we are" said Blaze, stepping through the door to her room, Mina and Tails following.

Tails looked over Blaze's room. It was just as he remembered the other rooms he had visited, though of course, it had been accustomed to Blaze's liking. He turned back to Blaze and Mina, who were patting Blaze's bed, motioning for him to lie down. He quickly obeyed and laid down on the comfortable bed. 'At least these two are more gentle than Fiona' he thought.

"Now just relax and let us work our magic" said Mina, as Blaze took four sets of handcuffs and used them to chain Tails's limbs to each corner of the bed.

The two of them made sure he was cuffed firmly to the bed, they had both already heard from Fiona that Tails had managed to escape from her restraints when he last had some fun with her, and were not going to give him the chance to do that again. Once they were sure he was secured, they stood at the edge of the bed and began to undress themselves while giving Tails seductive lidded eyes that made him slowly become aroused.

First they removed their shirts, their breasts swayed as they lifted them over their heads. Neither of them were wearing bra's, but he supposed he should have seen that coming. Blaze's breasts were even glistening a little from the sweat from her workout. The two girls then went to removing their lower clothing. Mina removed her blue shorts and Blaze kicked off her white ones. The two girls were now completely naked, and Tails's throbbing member was fully unsheathed and ready to play. The two girls eyed it seductively and moved closer to him.

"Mm, a lot of other girls said you were packing" said Blaze, giving his dick a few rubs.

"But we haven't had the pleasure of having a look for ourselves" said Mina, giving the tip a small kiss, earning a gasping moan out of the fox.

"Oh God" he moaned as the two of them began to gave it some attention.

"Do you like that Tails?" asked Mina.

"I...I do" moaned Tails, thrusting his hips up into Blaze's hand unconsciously.

"Then your going to love this" said Blaze, releasing his shaft and cupping her tits in her hands "Mina, you know what to do."

Mina mirrored Blaze's seductive smile and the two of them climbed onto the bed and laid on their bellies. They pressed themselves up to Tails's shaft and enveloped it in their breasts. They began to stroke his length with their tits, earning louder more needy moans out of the fox. They watched the big erection as it thrust in between their breasts, disappearing into their cleavage and popping out again. Each time it popped out they both either gave it a quick kiss or a lick, making him moan louder.

The mongoose and the cat continued this for a bit until they decided to try something to make the fox even hotter. They both made sure he was watching them, and then they closed in and kissed each other. It wasn't a gentle kiss either, both of them lashed their tongues out at each other, wrestling together, and they made sure that Tails could see the action unfold before them as they continued to stroke his length. 'Okay, that is hot as fuck' Tails thought as he watched them, moaning and thrusting into their soft tits as they stroked him.

Soon Mina and Blaze broke away from the kiss and continued to stroke Tails's cock with their breasts. They continued this for a while before slowing down and pulling their breasts away in a teasing manner, making the fox moan in discomfort. Their tit-fuck had gotten him so close to his inevitable orgasm, he was just about to release before they pulled away.

"Aw, were you about to cum?" cooed Mina, flicking the head of Tails's prick with her tongue.

"Ah, yes" moaned the fox, pulling against his restraints, but to no avail. Shocker.

"Aw, don't worry" said Blaze, leaning close to the fox's face and giving him a couple of sweet kisses across his muzzle "We won't leave you in pain. We'll let you cum. Ready Mina?"

Tails watched as Mina nodded to the cat. They leaned in close to his length and began to slather the whole cock with kisses, making the fox cry out as their soft lips kissed his length. Their kisses slowly got more intense as they parted their lips and stated to lick his cock, occasionally trailing their tongues to the tip of his cock to suck on it for a bit before going back to licking his erection.

"Oh wow" moaned the fox as the two girls continued to service him.

The two girls grinned at his moaning and doubled their efforts, licking more enthusiastically and taking turns deepthroating him. It was extremely difficult for Tails to hold back his orgasm when two skilled mouth's were working his length so well. The chains that restrained him clinked and creaked as his legs and arms pulled against them. Mina and Blaze would also occasionally de-attach their mouth's from his cock and suck on his balls, sucking on one each. They caressed them with their tongues and sucked on them with the force of a vacuum. Tails cried out louder as they worked their magic.

The room was filled with loud, wet, sucking noises and Tails's loud moaning. Blaze and Mina's lustful work were driving him over the edge. He couldn't take it anymore. With one last moan and one last thrust, he came. Blaze and Mina gasped in delight as they were hit by an onslaught of creamy cum. It hit them in their faces, landed in their mouths and fell into their breasts.

"Mm, that was quite a load" said Mina, licking some of it off her lips.

"It tastes nice too" said Blaze, scooping some off one of her breasts and licking it off.

"But perhaps we should give Tails here a reward for being such a good boy and letting us service him" said Mina.

"Not a bad idea" said Blaze, reaching down and rubbing Mina's pussy lips "You can go first if you like."

"Thank you" said Mina, gasping at Blaze's fingers rubbing her lower lips.

Tails watched as Mina straddled him and placed her hands on his chained arms. Her soaking pussy was right above his cock, ready to spear itself with it. Tails stared up into Mina's eyes, which were lidded and lust driven.

"Ready for the best part, big boy?" Mina asked in a husky voice.

"Y...Yeah, I am" said Tails, his eyes darting over every inch of Mina's sexy body.

Mina gave the fox a large grin and slowly lowered herself down. She teasingly rubbed her pussy against his cock just to get him more riled up than he already was. Tails whimpered slightly and thrust his hips without even controlling his own body to do so. The head of his cock was inside of Mina for a brief second. Mina's cheeky smile grew wider.

"Mina, come on" said Blaze, giving the mongoose's ass a slap, earning a moan out of her "We're gonna be here forever at this rate."

Mina gave a soft giggle and did what Blaze said. She lowered her hips down, slowly taking in the tip of Tails's dick, slowly making her way down. She moaned out at how it stretched her out and Tails moaned at how tight and hot her inner walls were, squeezing on his length. Soon, Mina and Tails's crotch's touched as Mina finally took his entire cock inside of her.

"Oh wow" she moaned "Nice and big. Just the way I like them."

Mina did not beat around the bush, she lifted her hips up while using her hands to keep Tails's hands pinned down, not that she really needed to do that anyway. Mina began to ride his shaft, driving it in and out of her quickly. She moaned particularly loud when the tip of his cock slammed as deep at it could go into her.

"Mm, that feels so good scraping inside me" moaned Mina "Fuck, your so fucking big Tails."

"Oh wow" moaned Tails "T...This feels amazing Mina."

As the hot action unfolded before her, Blaze began to get super hot and bothered. She wanted to get some action too, but with Mina occupying his dick, it didn't really give her a choice. But she could see that in all the hot intense pleasure, Tails's tongue had flopped out of his mouth. Giving her an idea, Blaze crawled over to Tails's head. The fox watched her as she lifted one leg over him and placed her soaking wet cunt right over his face. He stared at it in awe.

"Go on cutie" said Blaze "Get a nice good lick of me."

Tails didn't need a second invitation. As Mina continued to bounce on him, he dove his tongue into Blaze's pussy. He licked at her lower lips for a bit, making the kitty give several passionate moans, which only became more intense as Tails edged his tongue inside of her and began licking around inside her twitching inner walls. He twirled his tongue around in ways that made Blaze shiver above him. In all his excitement, he had not realised that he had begun to thrust his hips up into Mina, making his dick go even deeper into her when she thrust her hips down. He was timing their thrusts together perfectly without even realising it. Mina's moans reached a higher pitch at this.

"S...So good" she moaned, reaching up to play with her breasts. She rolled them in her hands, pinched her erect nipples and gave them a hard squeeze. Even with all his visual attention focused on Blaze's dripping pussy, Tails could still see her play with her breasts. He wanted to touch them so badly and do exactly what she was doing to them. But the fact that his arms were chained to the bed only made her hotter.

All three of them moaned together as they continued to pleasure each other. Mina kept thrusting her hips up and down, making Tails cry out at how tight she felt, as well as making her scream in ecstasy at how much she was stretched out. Despite the mind numbing pleasure Mina was making him feel, Tails had not once ceased his actions on Blaze, he made the cat squirm above him by dragging his tongue all over her sensitive lower lips, thrusting it inside her and licking her inner walls and occasionally closing his lips around her erect clit and giving it a couple of gentle licks. Blaze cried out at his actions and ground her hips into him, trying to force his tongue even deeper into her pussy.

All too soon, Mina could feel Tails's shaft begin to throb inside of her, which sent her a signal saying that he was getting close to his orgasm. She got excited and sped up her thrusts, wanting to cum with him. Blaze kept her hips firmly planted against Tails's face. Getting the hint, Tails began to lick her faster with more enthusiasm. All three of them were about to cum, and they didn't try to stop the mind numbing pleasure from taking over their bodies and plunging them into the pits of ecstasy.

"O...Oh God Tails" cried Mina "I'm cumming."

"Make us both cum Tails" Blaze gasped.

All Tails could do was release a very loud moan of pleasure, which was somewhat silenced by Blaze keeping his mouth against her pussy. He thrust his hips upwards into Mina, cumming deep into her. Mina cried out as her own orgasm crashed against Tails's cock and coated his crotch, all while feeling Tails's hot cum rocket up inside of her and filling her nicely and making her quiver. Blaze's own orgasm wracked her body and coated Tails's face with her vaginal juices. The fox didn't let it lie, he quickly got to work in licking his face and Blaze's pussy clean.

"Damn" said Mina, weakly lifting herself off of the fox "You are just as good as the other girls said you are."

"You've got quite a skilled tongue too" said Blaze, lifting herself off of Tails's face.

"Don't you want a go too?" asked Tails, looking at the sly purple cat.

"No, we were just going to remove the cuffs and send you on your way" Blaze said in a sarcastic tone.

"Sorry" said Tails.

"Don't be" said Blaze, crawling down the fox's body to take Mina's position. She turned around so that she was facing the fox, she positioned her hips above his still erect cock. Mina stood back and watched as the ordeal unfolded before her. Tails watched as the sexy cat prepared herself to take his cock into her pussy, which was now even wetter due to how he had made her cum earlier.

Unlike Mina, Blaze did not tease him to get him riled up, she usually would have, but Mina already did the job for her. Any more teasing towards Tails would be pointless if he was already hard as a rock and eager to please her. No, instead she pressed the head of his cock to her dripping lower lips and held herself there for a second before quickly dropping herself, taking his entire cock into her.

Tails and Blaze cried out as Blaze felt herself get stretched by his cock, and Tails felt her tight inner walls squeeze his length. But he also found the insides of Blaze's pussy rather hot. He then suddenly remembered why she was called Blaze, she could manipulate fire. Naturally this would make her body quite warm and another person would certainly feel it when they would come into contact with her. Thankfully it was not hot enough to burn him, rather it felt extremely nice to be nice and snug inside of Blaze's warm inner folds.

Blaze began to bounce herself up and down on Tails, making herself and the fox release loud orgasmic moans as they pleased each other. Tails gave a couple of thrusts of his own as his horny mind began to speak for him. But he couldn't help but stare up at Blaze's bouncing form, particularly at her breasts which swayed with each movement she made. Mina did not fail to notice at what part of Blaze's body he was staring at. Cracking a large grin, she crawled up to Tails and wrapped her arms around his head, pushing it into her sizeable breasts.

"Go on cutie" she said, giving his ear a gentle lick "You know you want to."

Tails couldn't help himself. He closed his mouth around one of Mina's breasts, trailing his tongue around the sensitive flesh at then flicking her erect nipple with his tongue. After he did that, he gently closed his teeth around it, carefully biting it and tugging it by pulling his head back. He then released her breast and moved to her unoccupied tit. His actions earned many sweet moans from the mongoose, who dug her fingers into his hair and whispered for him to do more.

Meanwhile, Blaze was still riding him. She groaned and screamed in horny bliss as she felt the fox's large cock scrape at her inner walls, causing her extreme pleasure that sent electric shocks down her spine. Her actions caused Tails to moan into Mina's chest as he was sucking on her breasts, which caused tiny vibrations that made his work even more pleasurable for Mina.

Blaze watched as Tails pleasured Mina's breasts. From what she could see, and from Mina's expressions, he was doing quite a good job. Wanting to see how good he was, Blaze pulled Mina away and fell on top of Tails, pressing his face into her own chest. Tails was not expecting this action from Blaze, but didn't complain and got right to work, causing Blaze to scream even louder as he performed the same moves on her breasts that he did with Mina, trailing his tongue on her breasts, flicking her nipples and gently biting them.

"Aw, come on Blaze" Mina pouted playfully "Don't hog him all to yourself, we shared him when it was my turn."

"S...Sorry Mina" gasped Blaze "He's just so good at this."

Tails blushed at this as he continued to work on pleasuring Blaze to the best of his abilities without having the ability to use his hands to make her feel even better. Soon though, Blaze was satisfied with how he sucked on her breasts and let Mina have him again. She sat up straight again and began to ride his shaft even faster, feeling her intense orgasm rushing forward.

Tails was close too, he felt his face get pushed back into Mina's breasts. He set to work immedietely as he continued the speed of his own thrusts upwards into Blaze. The chains strained against his arms and legs as he did his best to give Blaze an even more pleasurable experience.

It was pointless to try and prevent their inevitable releases. Blaze and Tails were right at the brink of cumming. Mina watched in awe, still moaning at Tails's impressive mouth work, watching the two of them descend into the pits of mind numbing pleasure.

"I...I'm nearly there Blaze" Tails cried from Mina's chest.

"So am I" gasped Blaze.

Blaze pressed her palms deeply into Tails's fuzzy chest and slammed her hips down against his one last time. Tails pulled at the chains as hard as the could and thrust his cock as deep as it could go. Blaze threw her head back and screamed in pleasure as she felt her pussy get filled with his warm cum. Her own vaginal juices splashed down onto his cock, making her shiver in pleasure as the two of them calmed down from their intense orgasms. Tails panted to get his breath back as he rested his head on Mina's chest.

"Wow Tails" Blaze sighed as she slowly lifted herself off of him "You are quite the stud that the other girls said you were."

"Hehehee, and your so cute too" giggled Mina, hugging his head into her chest more, making the fox blush. Even with a mind blowing time with these two, Tails knew it was only the beginning of his pleasurable adventures tonight.

Meanwhile, back in Rouge's office, Fiona and Rouge were talking to Rosemary. She had explained more in depth about what she was doing here, and they had to admit, it was not what they were expecting.

"So what your saying is, you want to work here for the night to 'spend time' with your own son?" Fiona exclaimed "Not gonna lie, that's a bit fucked up. Your his mother lady."

"Yes" said Rosemary softly "I know this is frowned upon, but I've been so alone for several years. My husband died 3 years ago and I don't just miss him, I'm so damn horny all the time, and well, I don't really want to start another relationship with someone I don't know very well. I mean, I'm not exactly looking to start a relationship with Miles, but, if he's made a name for himself here, then he must be quite a stud. I haven't had sex in a long time. I miss my husband, but for the longest time, I've had a void that needs to be filled, and, my son is the only one I trust to do that"

Rouge and Fiona just looked at the older fox woman. They were honestly moved by Rosemary's choice of words. Sure, neither of them could exactly how she felt, but it was hard to not sympathise for her.

"Hey, listen Miss" said Rouge.

"Oh dear, formalities aren't necessary" said the motherly fox "Just call me Rosemary."

"Okay, Rosemary" said Rouge "I understand just how sad you must be. I can offer you a one night job here for the night so you can spend time with your son, I can even pair you with one of my girls. And if it's your son you want, I won't judge. It ultimately comes down to how Tails feels though."

"You mean it?" asked Rosemary.

"Of course" said Rouge, wearing a sly smile on her face and reaching for her cellphone "In fact, I think I know just who to pair you with."

Rosemary and Fiona watched and waited as Rouge quickly dialled a number on her phone and waited for her employee to pick up and speak with her. After a few rings she picked up.

"Hello?" she said to them "Yes, could you come to my office real quick? I need your help with something."

**Notes for the Chapter:**

> Yes, there is going to be incest in this story. Now I want people to know that just because I write about incest I don't support it. I don't and I never will. But I will write the incest chapter because it is part of the request. But hey, if you don't like incest in fanfic's it's fine, you can just not read that chapter. I hope you all understand that I don't actually support incest and I hope you still enjoy what more this fic has in store.


	2. Rouge and Fiona

**Summary for the Chapter:**

> Remember, I am not actually stealing this from rdphoenix07 from Fanfiction.Net. If you are familiar with his work, than you know where I got the inspiration from this fic. Now then, I hope you enjoy this chapter. Also if you don't like incest, please do not read the next chapter as it will have an incest scene between Tails and Rosemary, but I'm sure you all knew that. But I cannot stress it enough when I say I don't support incest, and just because I write about it does not mean I support it. So please be respectful

Rouge, Fiona and Rosemary waited patiently for Rouge's employee to enter the office. After a little bit of waiting, a tall rabbit wearing a purple corset, purple gloves and brown shorts walked inside. Her corset struggled to keep her enormous breasts inside. Rosemary stared at the figure in surprise as she walked in, she had never seen a bustier, curvier woman.

"There you are Vanilla" said Rouge.

"Hello Rouge, Fiona" said the rabbit, nodding at the red vixen, she noticed Rosemary sitting with the two girls and was immediately curious "I don't believe we've met before. What's your name?"

"Hello, I'm Rosemary" said the mother fox, holding up her hand to shake hands "Nice to meet you. You may know my son, a young fox with nice manners and two tails."

"Your Tails's mother?" the rabbit said in surprise.

"Vanilla, I was wondering if you could help me and Rosemary with something" said Rouge.

"Yes... what would that be?" asked Vanilla, taking a seat of her own with Rosemary and Fiona.

Rouge, Fiona and Rosemary told Vanilla about Rosemary's needs and how she wanted to take her son tonight. Vanilla was surprised with Rosemary's story, but didn't judge her for her wanting to have sex with her own son.

"So what does this have anything to do with me?" asked Vanilla.

"Well, Rosemary here is going to work here for the night" said Rouge "And you know the rules of tonight Vanilla. Every customer gets to be dommed by two girls. And I know Tails does have a particular liking for you. So I figured you would be perfect to pair you with Rosemary."

"I think that can be arranged" said Vanilla, wearing a seductive smile, she turned to Rosemary "So Rosemary, are you ready to have some fun with your son?"

"Hold your horses" said Fiona "Tails made a promise to me tonight. He promised to come and see me."

"I think I know how we can go about this" said Rouge "Tails should be busy with Mina and Blaze at the moment. I'll call them to tell them to send Tails here. From there, me and you, Fiona, can have our fun with him. I was kinda hoping for a go with him myself. After we had our fun with him, we'll send him to Vanilla's room. While he's busy with us, you two can prepare yourselves for him. What do you all think?"

"I really like that idea" said Rosemary "It would give me and Vanilla plenty of time to set ourselves up for Tails."

"Good" said Rouge "But remember Rosemary, it's up to him whether or not he actually wants to have sex with you."

"I know" said Rosemary "But I'm going to try."

"Good luck to you then" said Rouge, winking at the mother fox "You two get going then. Vanilla, you still need to prepare her for tonight."

"I'm on it" said Vanilla, standing up from her seat and motioning Rosemary to follow her "Come with me. We need to pay a quick visit to Honey, we'll have to find an outfit best suited for you."

Rosemary nodded and stood up. The two milfs left the office and went to go prepare themselves for the two tailed fox, leaving Fiona and Rouge in the office.

"Now that that's sorted" said Rouge, turning back to Fiona "Let's plan out our little fun with the little fox."

"What did you have in mind?" asked Fiona.

"I recently had Honey make me some 'special outfits'" said Rouge, wearing a large sinister grin "And I think Tails would like to see them."

Meanwhile, back in Blaze's room, Blaze and Mina were cuddling with Tails. The two girls had taken off the handcuffs from his arms and legs and he was free to touch them as they lovingly cuddled and kissed him sweetly. They were gasping and moaning in his ears as he kissed and gently nipped at their necks and breasts, and used his hands to squeeze their tits and their rears. They pressed themselves up to him as they felt him caress their bodies.

"Oooh damn" moaned Blaze, as Tails dove his face into their breasts and sucked on them greedily "You really are a breast man Tails. Mm, so good at sucking on them."

"We'd love to have some more fun with you" said Mina "But personally, I wanna see just how good you are when your free to do whatever you want."

"I'll certainly come back again" said Tails, giving each of them another kiss.

Suddenly the three of them jumped in surprise as they heard Blaze's phone ring on her night stand. The cat reached over and picked up the phone to speak to the caller.

"Hello?" she said "Yes. He's still with us. Okay, we'll send him over."

She hung up and turned her attention to Tails.

"That was Rouge" said Blaze "Sounds like she wants you for something. She told us something about keeping a promise for Fiona."

"Oh yeah" said Tails, clapping a head to his forehead as he suddenly remembered "I did make a promise to Fiona. I should probably get going."

"Alright" said Mina, slightly disappointed that Tails was leaving so soon "Please don't be afraid to visit us again."

"Of course not" said Tails, kissing Mina again "I will definitely be coming back."

"Well our doors will always be open to you Tails" said Blaze, as the fox kissed her as well "But you better head off to Rouge's office while the night is still young."

Tails lifted himself off the bed, waved goodbye to the two sexy girls and left Blaze's room, closing the door behind him. He then made his way over to Rouge's office. Eventually he found it, two security guards stood in front of the door.

"Hey guys" said Tails "Rouge called for me."

One of the guards nodded and stood aside, opening the door for Tails to let him in. The fox walked right past and heard the door close behind him. Though, he was not really focusing on that, he was focusing on the fact that he had just walked into the office of the brothel owner, and there she was, sitting at her desk with Fiona sitting on a chair behind it. The two of them were anything but dressed appropriately.

The two of them were wearing black skin tight leather corsets that were secured tightly around their chests and pushing their breasts out to make them look bigger. Neither of them were wearing any thing below their waists, which showed off their shapely thighs and their soaking wet cunts. They were both wearing a black leather choker with a silver plate, the word 'Mistress' was engraved into these plates.

"There's our little two tailed stud" said Rouge wearing a large grin on her face.

"I knew you'd keep my promise" said Fiona, mirroring Rouge's smile.

"Come here Tails" said Rouge "Join us for a little bit of fun."

Tails wasn't even sure if he was in control of his legs as he walked towards them, they stood up from their seats as he got closer, Rouge stepped from behind her desk and stood at Fiona's side. Tails stepped directly in front of the two women, who were eyeing him like a delicious piece of candy. Without warning, Fiona and Rouge wrapped one arm each around Tails and both trapped him in a three way kiss. Tails's eyes widened and he gasped into their mouth's as they were pressed to his lips, which gave both of them an opportunity to insert their tongues inside of his mouth and wrestle him into submission with ease as it was a two on one. All Tails did was stand there in awe as the two skilled tongues lashed at his own.

Tails then suddenly jolted forward in surprise as he felt his arms suddenly get grabbed by the two sexy girls. He broke the kiss and turned his head to look behind him to see that they were tying his hands up with some rope. He gave a small yelp of pain as Fiona made sure the rope was tightly secured around his wrists, as he expected, she was making sure that he would not be able to escape this time.

As soon as Fiona and Rouge securely tied his arms, Fiona lifted him up with surprising ease while Rouge quickly removed any items from her desk that would be a nuisance. When she was finished, Fiona laid Tails on the desk and went down to his legs. She brought them together and began to use another bit of rope to tie up his legs so that Tails was trussed up like a turkey. Tails gave another small yelp of pain when Fiona once again tightened the rope around his ankles.

Then Tails's attention turned back to Rouge, who was holding something in her hands. Upon a closer look when Rouge got closer, Tails could see that it was a collar with a small metal plate loosely hanging from a ringlet on the collar, the plate had the word 'Pet' engraved into it. Tails watched as Rouge wrapped the collar around his neck and closed it.

"We were hoping our little pet fox would join us tonight" said Rouge, giving the fox a gentle pat on his head.

"W...What?" Tails asked in confusion "What do you mean Rou..."

"Ah ah" Rouge interrupted him by pressing a finger to his lips "Naughty pet. You won't be calling me by my name tonight."

"Huh?" asked Tails, tilting his head in confusion.

"You heard your Mistress" said Rouge "Tonight, you are our little pet fox. Be a good little pet, and we will reward you. Disobey our orders, and you will be punished. Understand cutie?"

"Err, maybe put a little more context into it?" Tails asked, trying to sound polite as he didn't like the sound of being 'punished'.

"Tonight, you will refer to both of us as 'Mistress'" said Fiona, giving Tails a pat on his head.

"Okay Fio... er, I mean Mistress" said Tails, quickly learning his place "But what exactly do I do?"

"Whatever we ask you to do Pet" said Rouge.

"But what would that have to do with... Oh" he suddenly gasped as he felt two gentle hands grasp his cock, which he had forgotten was fully erect upon seeing Fiona and Rouge's sexy outfits.

"If you do what we ask and do it well" said Fiona, giving the head of his cock a couple of nice, slow strokes "We'll reward you with pleasure."

"But at the end of the day" said Rouge "Your pleasure doesn't matter, it is only a reward if you pleasure us. And you will only be rewarded if you do it well."

"O...Okay Mistress" said Tails, getting a feeling that he understood completely now. Yes, he had taken a liking to bondage, but he wasn't sure how he felt of being treated and referred to a mindless animal. And yet, he couldn't help but also feel quite turned on and excited at the same time. Relaxing a little bit, Tails gave the two girls his full attention, showing that he was willing to listen to whatever they asked of him. They saw this all over his face and they grinned, they both leaned down and gave him several kisses on his muzzle.

"Good boy" they both whispered into his ear, petting his head and stroking his erection. Tails fidgeted in pleasure as he heard those words.

Fiona and Rouge began to slowly pump their hands on his dick, stimulating the fox. Tails groaned in pleasure at the feeling of their hands caressing his dick. He couldn't help but begin to start thrusting into their hands as best as he could with his legs and arms tied down.

"Ah, naughty Pet" said Fiona as she and Rouge suddenly stopped stroking his cock "We didn't say you could thrust did we."

"S...Sorry, Mistress" said Tails, his ears drooping and pinning to his skull "It just felt so good."

"Even so, disobeying your Mistress's is naughty" said Rouge "We'll need to make sure you don't do it again."

That was when Tails saw that in Rouge's hand was a cock ring. He watched as she placed it on his throbbing erection and locked it around the base, which would prevent him from cumming.

"If you disobey us again, that ring stays on as we ride you all night" said Fiona, giving his cock a nice squeeze.

"And for extra precaution" said Rouge, motioning Fiona to follow her lead.

The two women grinned mischievously at the twin-tailed fox and climbed onto the desk. They positioned themselves on either sides of his waist and pressed their dripping wet pussies to his throbbing erection. As if that wasn't enough to get the fox's rocks off, the two girls leaned in and started to kiss each other. Like Mina and Blaze, they made a point to show Tails their tongue's lashing out at each other, as well as groping each other's luscious bodies. As they passionately made out, they ground their pussies against his cock, covering it with their pre and making the fox moan out and squirm. But he tried his hardest to not thrust against them at the fear of being punished. By the time the two girls were done teasing him, his cock was so hard, he swore he could destroy a rock with it.

"Now, our little Pet won't thrust when he's not told to anymore will he?" said Rouge, looking down at the fox.

"N...No Mistress Rouge" said Tails.

"Good boy" said Rouge, giving Tails an affectionate scratch behind his ears.

"Now just sit back and let us call the shots" said Fiona, as she and Rouge climbed off the table "But no thrusting until we say you can. Got it?"

"Yes Mistress Fiona" said Tails.

Fiona gave the fox a sweet smile that seemed quite out of place for her and gave him a kiss on his small black nose. Rouge giggled in her usual sultry tone and climbed back over his body. She positioned her soaking wet cunt right in front of his face.

"I think we'll start off with this" said Rouge, reaching one hand down and spreading open her pussy lips "Lick here Pet."

Tails shuddered at how she addressed him. The way she said it with her tone caused him to feel a tiny bit afraid, yet, also very turned on at the same time. Surprisingly, he did not feel downgraded at being addressed as a pet anymore. Moving his face as close as he could to her pussy, Tails parted his lips and let his tongue flop out. He dragged across Rouge's lower lips and made the bat throw her head back and moan out at the feeling of his long canine tongue licking her. Her noises encouraged Tails to go deeper into Rouge's pussy. She gave another loud moan as she felt the wet digit insert itself inside her, licking all over her sensitive inner walls.

"Mm, good boy" Fiona whispered into his ear, causing the fox to shiver as he felt her hot breath tickle his ear "Eat her out like the good and loyal pet you are."

Despite the humiliating position he was in, Tails didn't mind. He was suddenly filled with a new determination, to please these girls and play his part as their submissive pet. It's what caused him to push his face as close as he could to Rouge's crotch and force his tongue as deep as it would go. Rouge cried out in pleasure and reached over to clutch at his head, trying to force his tongue inside of her more.

"Mm, that's a very good boy" Fiona cooed in his ear, Tails shivered again as he could feel the vixen's sizeable breasts, still restrained in her corset, press against his head as she spoke in his ear "Knowing his place and being such a good pet, pleasing his Mistress's."

"Oh fuck" cried Rouge, unconsciously bucking her hips into Tails's face "Oh your such a GOOD BOY, Oh DON'T STOP."

Fiona giggled as she watched Rouge's reaction's to Tails's intense and caring affection. It was really like he was trying to force her orgasm out of her. He had some really good oral skills, not many others could make her feel this way when they ate her out. Meanwhile, Rouge shuddered in excitement at the thought of how good Sonic, Knuckles and Shadow were at this, thinking of Shadow in particular. But tonight, it was just Tails, and she was still in so much pleasure it was almost felt like an overdose.

Tails was enjoying himself. Not only did Rouge's dripping orifice taste very nice, but the praise he was being given boosted his confidence, and left him with the satisfaction that he was pleasing the sexy bat. Fiona's words only egged him on as he delved his tongue as deep as it would go and traced it everywhere around Rouge's sensitive walls.

"Oh FUCK" Rouge screamed.

She was going to lose it at this rate. Tails's tongue just felt so damn good, it was impossible to calm herself down with how fucking good he felt. She couldn't stop the inevitable orgasm from approaching, not that she actually wanted to try. Tails just felt that good.

"FUUUUUUUUCK" she screamed, releasing a large squirt of her lady cum onto Tails's face. Tails, not expecting her to cum so fast from his oral work alone. He pulled his tongue out of her in surprise and flinched a bit as he felt a squirt of her vaginal juices almost hit him in the eye. As Rouge slowly came down from her intense orgasm, Fiona began stroking his ears again.

"Hey, you gotta clean that up, Pet" she whispered into his ear.

Fearing he would be punished if he didn't do as he said, Tails got to work quickly and began licking the cum off of his face, well most of it. His tongue may be longer than most, but it wasn't a tongue that belonged to a frog, and his face was completely covered with Rouge's lady cum, he could barely lick the liquid up from his chin. If Fiona wanted him to lick up every last drop, he feared the worst. Deciding that he would have to risk it, he went to lick up all of the juices that had covered Rouge's thighs.

"What's this?" said Fiona "You can't even clean up yourself. That's just a disappointment little pet."

Tails's large, triangular ears pinned themselves to his skull in slight embarrassment. He had not done as his Mistress had asked him, but what else was he supposed to do? However, he perked up a bit when he heard Rouge's sultry laugh.

"Oh Fiona, lay off him a bit" said Rouge, climbing off of Tails and petting his head affectionately "He's trying his best, and with his hands tied down, I think your asking for a bit much."

"I'm sorry" said the vixen, giggling in the same tone as the bat "He's just so much fun to mess with."

"Gee thanks" said a slightly grumpy Tails.

"What was that?" asked Fiona.

"I...I didn't mean that Mistress Fiona" Tails said quickly.

"Good, because you've 'cum' so far now" Fiona joked "I wouldn't want to end this with punishing you. Besides, you still owe me a good licking."

Taking Rouge's position on top of Tails, Fiona straddled him and pushed her crotch close to Tails's face. She placed his hands on the back of the twin-tailed fox's head and pushed his face right into her crotch, giving a slight gasp as she felt his warm lips press to her vaginal folds. Not even waiting for Fiona to give him a command, Tails parted his lips and delved his tongue deep into Fiona's cunt.

As Tails went to town on Fiona's pussy, desperate to please her, Rouge closed in from behind him and pushed herself up against the top of his head, making her large breasts press against his head, flattening his ears and making the fox look like he was wearing a pair of squishy earmuffs. She gave him a couple of kisses on his forehead as he continued to eat out Fiona.

"Don't mind her my little Pet" said Rouge in a soothing voice "Your doing just fine."

Tails gave a lustful, but submissive growl as he twisted and turned his tongue deep inside of Fiona's dripping cunt. Fiona twitched and fidgeted on top of him and dug her nails into the back of his head, scratching him, but he kind of liked it. Tails suddenly got an idea, he retracted his tongue from Fiona's cunt. Fiona was confused as to why he would stop, and super ticked off that he stopped in the first place. But before she could do as much as breath a word, her pupils suddenly shrunk and she threw back her head in blaring pleasure.

Tails had planted his lips on her pussy lips, kissing them, his lips had then identified the vixen's erect clit, the most sensitive part of her pussy. He gave it a couple of licks, which already made the vixen shake uncontrollably, and then attached his lips to it and began to suck hard on it. This caused Fiona to scream in pleasure as electrifying shocks of mind-numbing pleasure shocked and wracked her body.

"S...Such a good cunt-munching Pet" Fiona moaned, beginning to hump Tails's face without even realising it.

Rouge just smiled and watched Fiona descend into the pits of ecstasy and continued to make Tails shiver with want by rubbing her tits up and down his head. Feeling those soft, almost pillow like breasts rub up against him filled Tails with the urge to suck on them. While he was sure Rouge would like that, she had not given him the order to, and felt like he needed to either earn that or ask her, so he tried his hardest to keep his own urges at bay and focus on pleasuring Fiona.

If he didn't know any better he would say that she was getting so close to releasing. Her screams had pitched a higher volume and she was moving on top of him faster. If that wasn't enough of an indication, Rouge had also backed up to give them both some space. Wanting to bring the sexy red fox girl to her mind-shattering orgasm, Tails pushed his face as deep as it would go into Fiona's crotch, kept on sucking her erect clit, slightly grazing it with his teeth.

That was it. That was what pushed the fiery red vixen over the edge. She threw back her head, her hair flicking behind her head. Her tongue almost lolled out of her mouth and she used her fingers to really spread open her cunt lips and practically drench Tails in her lady cum. Tails didn't waste time, he began licking what he could reach while also having his mouth almost filled by Fiona's juices.

"Mm, I say you did a very good job at pleasing us, Pet" said Rouge, giving Tails another affectionate pat as he licked the juices off of his face "What do you say Fiona."

"He's perfect for a submissive role like this" giggled the red vixen "So obedient, so good. And so cute."

"Oh he most certainly is" said Rouge, tilting the blushing fox's head towards her's to capture his lips in a passionate kiss.

"M...Mistress Rouge and Fiona?" said Tails, after Rouge released him "I...I want to please you both."

"Oh? Well, we're interested" said Fiona, climbing off of him "So we'll hear your suggestion, but only this once."

"I... well... I want to pleasure... your breasts" Tails said, blushing hard. Normally he would be a bit more confident and just let the girls have it and go to town on their rack's. But since he was in this position, he felt like it would be better for him to ask, though it was still rather embarrassing. Especially when the girls began to laugh.

"Aw, our little Pet wants to suck on our tits" said Rouge "That would feel rather nice. But... it would also add to your pleasure, and that doesn't matter right now. But... Fiona, what do you think? Do you think we should let him take control, just this once?"

"Hm, well he has only made one tiny little error" Fiona teased "And he's pleased us thus far. So... I think we can let him play."

Tails watched as the two girls removed their corsets, when they took the restricting clothes off and tossed them to the side, their amazing tits bounced free. Rouge's obviously being the larger of the two, but Fiona herself was still quite well endowed.

"Alright Pet" said Rouge, as she and Fiona walked to either side of his face and pushed their big breasts into his face "All yours."

Tails eagerly got straight to work. He started with Fiona, placing his mouth over one of her tits and trailing his tongue all around the fleshy globe. Fiona moaned at this as Tails enclosed his lips around her erect nipple. He carefully nipped at it with his teeth and used his head to tug at it. He switched to her other breast and gave it the same treatment. Once he was finished, he moved on to Rouge. He gave her the same treatment as he gave Fiona, but spent a bit longer on her because of her larger breasts, which took him a longer time to lick all over because they were almost twice as big as Fiona's.

Fiona and Rouge moaned at his actions as he frequently switched between both girls, making sure he pleasured them both equally. To make him even hotter and more aroused, they pressed their tits up to him so that they were practically trying to crush his face with them. Meanwhile, they moved their hands down to his throbbing erection, which had yet to give up it's pent up release. They each wrapped a hand around it and began to stroke him, making the fox gasp and moan in pleasure, his noises muffled by their chest's. Though the need to thrust his hips into their hands was great, he kept his hips stable as he sucked on the girls amazing breasts, a task that was challenging, but apparently, not impossible.

"Mm, your so good at that Pet" moaned Fiona.

"Okay, okay" said Rouge, pulling away from Tails "I think we've kept him in torture for long enough Fiona. I think it's time he got what he truly came for."

"I agree" she giggled "Especially since he's been such a good boy. And good boy's always get rewards."

"Mmhmm" Rouge nodded with a huge grin on her face "Go ahead Fiona. Give him a fucking of a lifetime."

Fiona mirrored Rouge's grin and once again, climbed over Tails. This time she sat herself right above his crotch, her pussy positioned right above his throbbing cock, which had been teased to hell and back and was now likely harder than steel.

"Oh... Oh Mistress" he moaned, fidgeting as Fiona teasingly rubbed her cunt lips against his tip.

"Mm? Is there something you want to tell me Pet?" she said, leaning close to his ear and giving it a sensual lick and whispering hotly into it "Go on. Say what you want from me, and I will reward you."

"AH" he cried, feeling her hot breath and wet tongue touch his twitching ear "PLEASE! Please Mistress Fiona. Please ride me hard and fast. I'm so hard. SO FUCKING HARD!"

Fiona giggled at this, and so did Rouge as she was watching the ordeal in front of her. His desperate begging was really cute, but it also made Fiona feel so hot, she wanted to give Tails what she wanted, though her persona said she was just in it for herself. It didn't matter either way, because at the end of the day, both would get what they wanted.

She stopped teasing him and pressed the head to her pussy lips, slowly taking it inside. Both of them released a passionate moan as Fiona took Tails's hard erect cock into her tight, slick, inner folds.

"Mm, you can thrust your hips now, Pet" Fiona growled sensually into his ear "Make us both feel even better."

Being given permission to finally give into his own desires, Tails began to thrust his hips up into Fiona. It was difficult to do since his arms and legs were bounded, but he still managed. His efforts still made Fiona's moans peak a higher volume. Loud, wet slapping noises were filling Rouge's office as Fiona went at it with Tails, slamming and grinding her hips against his own and squeezing his cock with her tight inner walls, all while feeling his amazing length pound and pummel her pussy into mind-numbing oblivion. Both of them moaned out louder and louder with each passing second.

"Oh fuck" cried Fiona "That's it. Just like that."

"Oooohhh God" growled Tails, bucking his hips on instinct.

Fiona couldn't help but grope at her own breasts as she felt Tails's dick slam deep inside of her. Tails's eyes locked onto the vixen as she squished her sizeable tits in her hands and moaned out. He so wished that those were his own hands that were groping her breasts, but they weren't and his actual hands were tied up, and being denied the opportunity to touch Fiona only made her sexier.

Even though it did add to her already mind-numbing pleasure, Fiona was doing this on purpose because she knew it would 100% get him even more bothered and horny than he already was, if that was even possible. Yet, it also made his thrusts into her cunt even stronger. It was like he was trying to punch her orgasm out of her with his cock. It was getting to a point where it was impossible to keep herself from cumming, and her tight inner walls weren't doing Tails any favours in preventing his own orgasm either. But why would either of them want to stop it?

"A...Are you close?" Fiona gasped to him.

Tails didn't have the mind power to form a coherent sentence. He just clenched his eyes shut threw his head back and released a strangled cry which made Fiona grin mischievously as she could definitely take that as a yes.

"So am I" she cried to him "Release with me now, Pet."

That was it. Both of them gave the hardest thrust they could and released all over each other. Fiona cried out loudly as pleasurable electric shocks were sent through her body through the many shots of cum that rocketed into her body. Tails released a loud noise that sounded like a mixture between a moan and a growl as he felt the vixen's tight inner walls squeeze his throbbing length, milking out his cum as he felt her juices cover his cock, crotch and thighs. It felt like over a century before they calmed down from their orgasmic highs.

"Mmmhmm, sooo good" the vixen moaned, swaying a little on Tails before collapsing atop of him.

"Wow Pet. Impressive" said Rouge, walking over and shaking Fiona's shoulder "You knocked her right out."

"She did that last time I was with her... twice" said Tails.

"Really now" said Rouge, intrigued that this was not Tails's first time fucking Fiona to sleep "Perhaps there's something about you that has this sort of affect on Fiona."

"Or maybe she just get's sleepy after sex?" suggested Tails.

"Either way, it's my turn now" said Rouge, lifting the sleeping vixen off of Tails and his cock. A large amount of mixed cum leaked from the red fox's pussy as she carried her away to her bedroom that was just next to her office and then returned to Tails.

"Where'd you take her Mistress Rouge?" asked Tails, lifting his head to look at her.

"Oh I just laid her down somewhere more comfortable" said Rouge, excited that she now had Tails all to herself now "But now it's time I show you what I've got little Pet."

Rouge placed her hands on Tails's shoulders and pulled herself up onto her desk and straddled him. Taking the same position that Fiona did earlier by positioning her cunt right above Tails's cock, which was still throbbing hard and ready for another round. Tails's attention was only focused on her, his gaze darted towards several parts of her body. No doubt in Tails's mind, Rouge had a body and a figure that several girls, especially most of her employees, would kill for. Large bulbous breasts that almost seemed an impossible size, a nicely shaped ass, a gorgeous curvy figure. On top of that her large sensitive ears and scary looking bat wings added more character to her that made her extremely hard to not look at. There was really only one other woman who could top her.

He was so entranced by Rouge's form that he did not notice until she had slammed her hips against his that she was rubbing his tip against her vaginal folds. His eyes widened and he gasped out as he was once again enveloped by a warm, tight snatch. Rouge grinned at his expression and gave a sweet moan of her own as she was filled with the fox's rock hard dick.

"Mmm, you know Pet" said Rouge "I haven't had the pleasure of having some fun with a customer yet. I'm so glad that you could fill that void."

Tails's only response was to moan hotly as she began to ride him with proud vigour. Tails was almost mesmerised by Rouge's bouncing form and she knew he was staring. Like Fiona, she reached her hands up to her ample breasts and began to squeeze and play with them, just to get him more hot and bothered. She pinched her erect nipples in between her fingers, which caused Tails to whine and begin to thrust his hips upwards, timing his thrusts with her own, which caused her moans to reach a higher volume.

"Ah, Pet" she cried "So good. Mm, you deserve a treat for being such a good little pet for us."

Rouge stopped massaging her tits and leaned down to Tails. She pushed her big, round breasts into his face. Tails didn't need her to tell him what to do. He parted his lips and began to suck on them. Rouge began to moan sweetly as she bounced on him, feeling his warm, wet mouth caress the round orbs and feeling his tongue lash over them, using her hands to push him in deeper as he couldn't use his own.

"Oooh so good" she moaned, bouncing on him harder, falling in love with the feeling of his big cock scraping her inner walls.

Determined to please the brothel owner, Tails began to thrust harder into her and gently nip at the bat's erect nipples with his teeth, careful not to hurt her with his fangs. He got the reaction he wanted out of his mistress and she cried out, nearly screaming in pleasure as he speared her as hard as he could. It wasn't quite enough to make her scream, but he felt like he needed his hands free to reach that point. At the same time though, it was satisfying to hear Rouge's cry's of pleasure.

Besides, it looked like she was about to scream from pleasure anyway. He could tell she was getting close to her inevitable orgasm as her tight inner walls were becoming tighter and tighter. His own orgasm was approaching fast ad his shaft began to throb. Rouge bounced on him harder, wanting both of them to last as long as they possibly could.

"YES TAILS" she screamed, feeling her lady cum cover Tails's shaft.

"OOOOOHHH GOD" shouted Tails, feeling Rouge's juices cascade on his shaft and crotch as his own cum rocketed out of his cock and shot deep into Rouge.

Rouge shivered and cried out in heart-stopping pleasure as she felt the fox's creamy cum shoot inside of her and fill her pussy. She rode out her own orgasm as she felt the satisfying warmth spread through her.

"Mm, that was good fun. Wasn't it Pet?" said Rouge, only for Tails to not say anything "Tails?"

Looking down into the fox's face he could see that his eyes were shut and he had fallen asleep, clearly exhausted. His breaths were big and heavy, tired and exhausted from what he had just experienced. Rouge grinned at the sleeping fox.

"Looks like your worn out too" Rouge said to Tails, who was obviously not listening "I guess sex just makes foxes sleepy" she gave a small giggle "Your so cute when your asleep Tails."

Rouge climbed off of the fox, letting their mixed cum pool out of her and began to untie the rope from his legs. When she was done, she untied his hands. She then placed her hands over his neck and removed the collar from his neck. She hoped when he woke up he would still have the energy to go for one more round with Vanilla and Rosemary. She she carried him back to her bedroom where Fiona was currently sleeping, she couldn't help but wonder what the two of them were up to right now.

"Alright here we are" said Vanilla stepping into her room, carrying a new outfit that Honey had made for her. Rosemary followed suit inside of Vanilla's room, marvelling at it. She stepped inside and closed the door behind her.

"It was very nice of Honey to make this for me" said Rosemary "She practically had it at the ready like she knew I'd be here."

"Fashion is kind of her thing" said Vanilla "In fact, she made several outfits for my daughter Cream, for erotic cosplay."

"Wow" said Rosemary, impressed that this rabbit's daughter not only worked here, but had a kink for playing different roles during sex. She could only wonder what sort of outfits Cream had in her room to wear and treat customers with.

"Now, enough about that" said Vanilla, removing her corset and letting her monstrous tits bounce free "We've got to prepare ourselves for your son. He could be here very soon."

"Yes, of course" said Rosemary, quickly unbuttoning her blue dress.

She took a couple of deep breaths to compose herself. She was mere minutes, maybe even seconds away from meeting her son in such a place. She started to wonder if her son would be ashamed of seeing her in this place. NO! She shook her head. Tails loved her and would most definitely not think differently of her upon seeing her here.

Of course, she was stepping over a line that shouldn't be stepped over, but seeing Fiona, Rouge and Vanilla not holding a grudge against her, she wasn't as scared as she was before. It all came down to Tails, and she wasn't looking to start a relationship with her own son. No, that didn't seem necessary. She needed to relieve herself from this sexual itch that had been bugging her for far too long, and she was not comfortable with having a random stranger do it. She would only put her trust into two people, her husband, who could no longer provide that since he had now passed away, and her son, a person who she shouldn't turn to, but she knew very well.

Yes, it was wrong. But people around her were not holding it against her, they even seemed to understand and sympathise for her. She was more comfortable with doing this. The only thing that would put a stop to this would be Tails's refusal. 'I really hope he's okay with it' she thought to herself.


	3. Vanilla and Rosemary

**Summary for the Chapter:**

> WARNING! WARNING! THIS CHAPTER CONTAINS INCEST BETWEEN ROSEMARY AND TAILS. IF YOU DON'T LIKE INCEST THEN DO NOT READ THIS CHAPTER! I just want people to know for like the millionth time that I don't support incest in real life, and just because I write about it doesn't mean anything. Continue reading if you want, but please do not attack me for an incest scene. If you don't like incest, then don't read. It's very simple. That goes for all of my fics in general.

Tails awoke with a shuddering yawn. He had never felt so tired in his entire life. He snuggled into the blankets and pillows of the bed, wanting to return to dream land. But just as he was about to nod off again, he was shaken awake by someone shaking his shoulder.

"Don't fall asleep on me again foxy. The nights still young" a voice rang in his ear.

Blinking his eyes and scratching the back of his head, Tails slowly sat up and looked around. Upon realising that he was not in his bedroom, his memories flooded back into his mind. Looking to his sides, he could see Rouge and Fiona next to his sides, looking up at him with seductive expressions.

"Have a nice snooze?" giggled Rouge.

"Y...Yeah" said Tails "S...Sorry, I didn't mean to fall asleep."

"Relax honey, neither of us are offended" giggled Rouge "Now I was wondering if you could do me a favour?"

"Oh? What?" asked Tails.

"Remember Tails, you get to be entertained by three pairs of girls tonight" said Rouge "You still have one more pass before you can leave. And Vanilla called me before I sent for you. She wanted to spend some time with you."

This was partially a lie. Vanilla didn't call her, she called Vanilla. It's not that Vanilla didn't want to see Tails, but if Rosemary was going to get what she wanted, then Rouge would have to lie to the fox, which she didn't like doing. But it wasn't going to hurt him, besides, the best lies are those sprinkled with the truth.

"She did?" asked Tails, remembering the first time he was with Vanilla. That rabbit had curves for days, she was easily one of his top favourites at the brothel. How could he refuse this? Plus another girl would be with her? That was a serious score. The girls giggled as he practically leapt out of the bed.

"Hey" said Fiona "Aren't you going to say goodbye to us?"

"Oh sorry" said Tails, embarrassed that he let his excitement get the best of him and forgot his manners "I'm sorry if that looked immature, I do like you girls too. I..."

"It's okay sweet stuff" said Rouge, holding up her hand "You came here to enjoy yourself. So go enjoy yourself. Just don't forget to drop by again when you come back another time."

"I promise" said Tails, giving the girls a kiss on the cheek.

The two of them watched as the two-tailed fox left the room, on his way to Vanilla's. If they were being honest, both of them felt rather nervous for Rosemary. This was it, this was the final step. If Tails refused, then all the work they put into this plan would have been for nothing. They would understand if Tails refused of course, it was frowned upon to engage in sexual intercourse. But Rosemary needed this, and she didn't trust her feelings with anyone else but her son. In the end, it was Tails's choice, and the two of them hoped he would make a good one.

After a little bit of walking, Tails had reached the room of Vanilla the rabbit. As stated earlier, Vanilla was easily the bustiest female in the entire brothel. It excited him that Vanilla wanted to see him tonight. He knocked on the door and waited for the rabbit milf to open up. The door creaked open and there she stood, the curviest employee in the brothel by far, Vanilla the rabbit. Tails nearly got a nosebleed from what she was wearing.

The rabbit milf smiled down at him with a kind, almost motherly smile, with a hint of saucy mischief behind it. But what she was wearing was what caught his attention. She was wearing a yellow lingerie that was a couple of sizes too small for her. It really emphasised the size of her breasts, they stretched out the fabric to the point where it looked like the slightest movement would cause it to rip. Her belly was completely exposed and the panties she wore clung to her body like a second pair of skin. It really did nothing to hide her massive ass.

"I was expecting you" said Vanilla, giving a slight shake of her body to entice the fox.

Tails looked away, slightly embarrassed by this. Vanilla only giggled and took him by the arm and brought him inside her room, shutting the door behind her.

"Now, now Tails" said the motherly rabbit "There's no need to be embarrassed. You've seen all of me before haven't you? So why should you cover your eyes now?"

"Sorry" said Tails, seeing logic behind her reasoning "It's just... I wasn't expecting to see you dressed like that. Can I say, it really makes you as beautiful as it does make you sexy."

"Oh you flatterer" giggled Vanilla.

"So I know you wanted to see me" said Tails "And I know the rule is two girls pleasure me. But, I don't see Cream here."

"Oh... no little fox" giggled Vanilla "Cream's not going to be joining us."

"Why not?" asked the fox, who really thought Cream was the obvious choice.

"Because I have someone else in mind" said Vanilla "Someone who has shown a particular interest in you. But before I show her in, I'll need to tie you down to my bed."

Tails decided to not argue, even though he wanted to know who this mystery girl was that Vanilla had in mind. He walked over to her bed and laid down in an X position, giving Vanilla an easier time to tie all of his limbs to the bed. He flinched in pain as he felt the rope tighten around his wrists and ankles. Vanilla noticed this and kissed his forehead with a motherly attitude and smiled sweetly at the fox.

"Now you just wait here while I go get my friend" said Vanilla, stepping out of the room.

Tails waited patiently for Vanilla to return. He wondered who Vanilla was going to get. There were so many other girls other than the four he had just been with. Rouge, Fiona, Blaze and Mina were out considering he was just with them, and Cream was also out since Vanilla deconfirmed it herself. He knew about all the other girls who worked here, just who was Vanilla going to bring in. The remaining options were Sally Acorn, Nicole, Amy Rose, Julie-Su, Hershey, Honey, Tikal, Cosmo, Marine, Lupe, Sticks, Lien-Da, Shade, Lara-Le, Tiara, Aleena, Sonia, Bunnie and Tailsko, a female fox who looked exactly like him for reasons no one knew why.

All of these girls were extremely hot and alluring in their own way, practically anyone who joined Vanilla would be fine by Tails. Then again, perhaps a new girl had just joined tonight and were beginning their work with Vanilla as their mentor. He was about to find out just who would be joining him and Vanilla, as he heard two pairs of footsteps returning towards him. Vanilla walked into the room, along with someone behind her. His eyes immediately shrunk in surprise and shock as he looked the figure up and down.

It was his mother, Rosemary. This was the last person he was expecting. He stared at her with a mixture of horror, and slight arousal. She was basically wearing what Vanilla was wearing, except her's was blue. She was not staring at him with a look of seductiveness, but rather a slightly nervous expression, with a bit of excitement as well.

"Hello Miles" she said.

"M...Mom?" he said, staring at the vixen "W...What're you doing here."

"Looks like we have some explaining to do" said Vanilla "Rosemary, why don't you tell your son why your here."

"D...Did you come here to have sex with me?" said Tails incredulously "NO! I don't want to, let me out."

This had turned from a dream, into a nightmare. He was fine with having sex with anyone, even a girl who had a rather unsettling look alikeness to him. But when his own mother was being presented, that's where he had to draw the line. He struggled against his bonds, not wanting to do this.

"Miles, just listen to me" said Rosemary "Please just hear me out before we let you go."

Tails stopped struggling and looked up at his mother with a look of disapproval. He wasn't exactly mad that his mother was working here, it was moreso that she was here to have sex with him. To step over a line that should never be stepped over. Rosemary saw this and her look changed to one of sadness as she walked over to the younger fox and knelt down on her knees next to a bed. She put an affectionate gentle hand on his head, asking for Tails to look at her. He did, but he still looked reluctant to go forth with what was clearly being implied.

"Listen Miles" said Rosemary "I know this is wrong on so many levels. But... ever since your father passed away, I've just been so lonely by myself with no one to help relieve the fire within me."

Tails's own look softened as she mentioned Amadeus. He missed him too, but he didn't even think about how much this would affect his mother. Not only would she miss him just as much as he did, but she would also have no one to scratch her itch whenever she needed it. It felt weird to think about his parents like that, but it suddenly made him feel sorry for his mother.

"Then... why didn't you just go... find another lover?" asked Tails, his expression softening as he looked at his mother.

"Well, you see Miles" said Rosemary "I don't think I want a new lover. At least not yet."

Tails sighed with relief. So that wasn't the reason why she was here with him. But she still clearly wanted to have sex with him. Even though Vanilla seemed nonchalant about this, meaning she wasn't judging Rosemary for her choice. But it was still just too weird for him.

"But my itch is just driving me crazy Miles" said Rosemary "But... I don't trust anyone else to help me scratch it without using me. I think sex should be meaningful and for enjoyment from both sides. And I only put that trust into two people. Your father, who sadly cannot provide that anymore. And you Miles. I know this is wrong, but you've always been so sweet and kind. And when I heard you were visiting this place. I thought this was the opportunity for me to finally relieve myself. And when I heard from Vanilla and a select couple of other girls about how good you are, I just know your good for me."

Tails stared up at his mother at surprise. Even though he was reluctant to do this at first, he had to admit. His mother's story was very touching and had moved him. How could he leave his mother in pain like this? If Amadeus was still alive, she would have probably turned to him to help her. But now he was dead, and thus, he was the only person she trusted.

"Look Tails" said Vanilla, stepping in "I know it's hard for you to have sex with your mother. But just look at how horny and desperate she is. But she doesn't want straight sex Tails. She wants love. And while she's not looking for a relationship with you, I know she loves you Tails, and you love her back."

Somehow, both of their words resonated with Tails. He looked back up at his mother. She was relieved to see that he no longer looked reluctant. Rather, he looked eager to please her and make her feel something she hadn't felt in years.

"Mom" he said "I'm sorry... for just shouting you and Vanilla down for not wanting to have sex with you now. Even though this is a line that's never to be crossed, I would be happy to make you happy. Because that's what I want you to be."

Rosemary didn't even respond. She took her hands and placed them on her son's cheeks and pushed her lips against his. Tails's eyes widened in surprise as her mother kissed him. He was given kisses by his mother before, but not like this. Yet, it felt so good. He kissed her back, wishing his hands weren't tied down so that he could wrap his arms around her, to hold her, to please her. She soon broke the kiss and looked at her son, this time with a more seductive, predatory look.

"I know I said I wanted to do this to make me happy Miles" she said "But I'm still your mother, and you need to be punished."

"WHAT!?" yelled Tails, perplexed that her mother had poured her heart out to him and was now punishing him for seemingly no reason.

"I didn't raise you to go into places like this to sneak your hands into a girls panties" giggled Rosemary "You naughty boy."

Tails eyes shrunk suddenly. This was true.

"W...Wait" said Tails "It wasn't my idea. I swear Sonic, Shadow and Knuckles dragged me here."

"Oh Tails" giggled Vanilla, stroking the fox's head "You take everything too seriously. She's only playing."

"Yes" giggled Rosemary "After all, it shouldn't just be meaningful. It should be fun too."

"Oh" said Tails, blushing and remembering that Rouge and Fiona kind of did this as well "Right."

The two milf's gave a couple of laughs and stood up, letting Tails see all the goods. Getting past the fact that Rosemary was his mother, Tails had to admit, she was definitely alluring. Her lingerie, like Vanilla's, was too small for her, making it cling to her body and make all of her curves sexier. Her breasts, while not as big as Vanilla's, were still nice and big and he was certain his whole hand would not be able to wrap around one of them. Vanilla of course, was still as sexy as ever, with breasts not many others could compete with.

Both of them were wearing sultry looks, clearly showing that they were serious. Both of them were sexy as fuck. They had wide, curvy hips, sexy breasts barely covered by their lingerie's and there were dark patch's slowly growing in the middle of their panties, indicating that they were getting wet.

"As punishment, me and Vanilla are going to have a ton of sexy fun without you" Rosemary said in a teasing manner.

"Sorry Tails" shrugged Vanilla "I would pleasure you. But Rosemary is your mother, and if she's punishing you, then you have to take it like a proper man."

He knew this was just an act, but this was still truly cruel. Being tied down to a bed, unable to move and forced to watch these two pleasure each other without getting some action himself was torture to a man, he was no different. Yet, their words seemed to give his dick a positive reaction as it was now standing at full attention, not unnoticed by the two sly milfs.

"Maybe if your good and take the punishment well, we will reward you" said Rosemary, running a single finger over his erection.

Luckily, Tails was just with Fiona and Rouge, meaning he knew that they were saying the truth. If he did as they say, he would be rewarded with pleasure. It was a little mean but oh so hot and sexy.

Stepping away from Tails, the motherly fox and rabbit placed their hands on each other's shoulders, closed in and locked their lips together. Like every other pair Tails had joined tonight, Rosemary and Vanilla made a point to make sure Tails could see their tongues dance together. Unlike the other pairs of girls, Vanilla and Rosemary were more grabby. A few seconds into the kiss, their hands trailed away from each others shoulder's and both of them began to grope at each other's bodies. They squeezed each other's hips, tails and ass's through the fabric of their panties, even shifting their tops aside so they could grope each others breasts.

Tails's mouth was agape as he watched the two sexy milf's make out with each other. It was one thing to watch two girls kiss each other, it was another thing to watch two milfs make out with each other, but this took the cake. One milf being impossibly busty and curvy make out with another milf, while not quite as developed was still sexy in her own right, being his own mother just made his dick throb harder than ever before. This did not go unnoticed by Vanilla or Rosemary as they grinned upon seeing the fox's large dick twitch madly, begging to be put to use on both of them. 'Mm, Vanilla and some of those other girls were right' thought Rosemary 'My son is packing. I'm getting hotter by the minute.'

Rosemary and Vanilla could feel each other's heat as they pressed their bodies together, and it only made them more hot and bothered. Both of them were tempted to drop the 'punishment' and have their way with Tails, but their plan was already working the way they wanted it to. He just needed a little bit more and he would be golden.

Tails continued watching in awe. He watched as the slightly shorter Rosemary wrapped one of her thick thighs around Vanilla's thicker thigh, watched as the two of them squished their breasts together, watched them wrestle for dominance with their tongues, watched Vanilla grope hard at Rosemary's rear with one hand while the other ran up and down her spine, and watched as Rosemary dug her fingers through Vanilla's hair. 'Are these two trying to turn my cock into steel or something?' thought Tails, who felt harder than he ever did in his entire life.

Both Vanilla and Rosemary pulled away and looked at Tails with lidded, seductive, hungry eyes. A string of saliva hanging from their lower lips was still keeping their mouth's connected. They could see that Tails was already extremely hard, and both were eager to jump it right now and ride him all night, but they knew that if they teased him for just a tiny bit longer, they could make it the best fuck of their lives.

"Rosemary" said Vanilla, turning to the slightly shorter fox "Could you follow me."

"I would love to" said the brown fox.

The two sexy AF milf's walked over to the couch in Vanilla's room, swaying their hips as they did. Vanilla laid down on the couch and Rosemary laid on top of her. The motherly fox slowly inched her hands towards Vanilla's stomach, trailed her fingers down to the rabbit's crotch and slowly inched them inside the thin lingerie panties she was wearing. Vanilla suddenly jerked and cried out a bit as she felt Rosemary's gentle fingers brush across her pussy.

Even though Tails couldn't see his mother's fingers past the fabric of Vanilla's panties, he could tell she was slowly inserting them inside her pussy because of the way Vanilla was squirming. He watched as Vanilla did the same thing to Rosemary, making the fox shudder on top of Vanilla as she felt the rabbit's fingers slowly force their way into her cunt, her long bushy tail flicking from side to side erratically.

The two mothers locked lips again and began to tussle again as they fingered each other. Even though this was an attempt to tease Tails even further to assure them a better fuck, this was also a small friendly competition between the two on who could cum first. Vanilla did have an advantage considering that she had been exposed to more treatments like this than Rosemary had. Though Rosemary was inexperienced when it came to pleasuring another girl, she wasn't bad as her enthusiasm was working out for her and making Vanilla squirm just as hard as she was.

All Tails could do was watch as the two sexy milf's continued to finger fuck each other, while pressing and grinding their luscious bodies against each other. Tails gave a small grunt. His erection was now so hard, it was painful. He wished that these two would just hurry the fuck up and stop teasing/punishing him and relieve him of this pain.

To her own surprise, Rosemary ended up cumming a couple of seconds after Vanilla. Vanilla broke the kiss and threw her head back as her juices completely soaked and ruined her entire lingerie and even squirted onto Rosemary. Her own hand was rubbing Rosemary's clit hard and fast, which in turn made the fox mother cum too, she soaked her entire attire and Vanilla as they came all over each other.

"Oh wow" moaned Vanilla, as they both calmed down "That was certainly exhilarating."

The two milf's turned to Tails. The twin-tail was fidgeting uncontrollably, the rope straining against the sides of the bed, his twin tails swaying up and down, smacking the bed below him with force he didn't know he possessed.

"I think we teased him enough Rosemary" said Vanilla.

"Yes" said the brown fox "Any more teasing would just be being mean at this point. Let's help him relieve all of that pain and stress built up within him."

"Let's lose the lingerie's as well" said Vanilla "Their ruined now, and we won't need them for what we're about to do."

Tails watched as the two milf's removed their attire and walked back towards him. His patience was about to be rewarded, he stared at their exposed bodies, looking like he was ready to pounce on them and have his way with them, which he would have done if he wasn't tied up.

Vanilla and Rosemary walked over to either side of the bed and knelt down, facing his monstrous erection. They both reached a hand out and began to rub his shaft up and down. Tails gasped and groaned in pleasure as the two lovely ladies stroked him, feeling a little of his tension leave. He eyed the soaking lingerie's on the floor, wanting answers to the question floating in his head.

"Where did you two get those outfits anyway?" asked Tails, grunting as both women gave his cock a little squeeze.

"Oh, we had Honey and Hershey make them for us" said Vanilla "You know how they are with fashion. After all, you saw all of my little Cream's outfits didn't you?"

"Yeah" Tails grunted, thrusting his hips unconsciously into their hands, making them stifle a laugh at his cuteness "I did."

Tails had a hunch that the outfits he saw Rouge and Fiona wearing when he went to visit them were also made by Honey and Hershey. He had a right mind to go and thank them for making tonight even more interesting and fun for him. But first, he had these two horny milf's to please.

The motherly fox and rabbit stopped stroking his cock and held it firmly in their hands, their other hands going towards the fox's plump balls and giving them a little tickle, making him groan louder. The two of them spat on his cock, lubing it up and using their hands to spread their wet saliva all over his dick. When they were finished, they both drew their hands back from his crotch and held the fox firmly by the hips to stop him from thrusting. Vanilla then leaned over, enveloped the head of his prick into her mouth and began to coat it with more of her drool, as well as roll her tongue around the entire shaft and suck hard on it. She thrust her head up and down on it a couple of times and then pulled away, giving Rosemary the opportunity to do the same. However, Rosemary did something else to pleasure her son. While her movements mimicked Vanilla's, she also carefully grazed her fangs against the fox's cock, making him shiver pleasantly.

For a while, the two of them continued to pleasure Tails this way. Taking in turns in deepthroating his cock, Rosemary and Vanilla showed off their amazing oral skills. While Rosemary might have not done this for a long time, her previous experiences with Amadeus stayed rooted into her memory and she still knew just how to please a man, and it looked like she was doing a good job based on her son's glazed, pleasured expression. Tails groaned as he felt their tight throats wrap around his cock, dug their tongues into his tip and suckled hard on his dick, tasting his delicious pre. Tails's ears pinned to his skull as the two sexy women orally fucked his cock, they both felt so good.

Rosemary was enjoying herself immensly. She may not be feeling too much pleasure herself, yet it still felt so nice to just pleasure a male. And the fact that it was her son made it rather erotic. Then suddenly, she was struck with an idea that made her grin, she turned her attention to Vanilla, who was currently having her turn in deepthroating Tails.

"Hey Vanilla" said Rosemary, getting the rabbit's attention, she looked up at the brown fox "Why don't we do something that Amadeus used to like on my son?"

"Oh? What?" asked Vanilla, making a sloppy sound as she pulled off of the fox's cock.

"Just do what I do" said a grinning Rosemary.

Rosemary leaned in and began to lick up and down her side of her son's cock. Following suit, Vanilla did the same to her side of Tails's dick. While Tails moaned at the two skilled tongue caressing his cock, Vanilla watched as Rosemary gently grabbed one of her son's tails. Vanilla grabbed the unoccupied one and continued to watch Rosemary's actions so that she could mimic them. The two female's began to stroke the smooth fur of his tails, making the fox quiver in pleasure for them.

Tails growled and groaned as he felt his orgasm approaching, and Vanilla and Rosemary could feel it as his shaft throbbed in their mouth's. Rosemary then made eye contact with Vanilla to make sure she was following her. The rabbit nodded and Rosemary wrapped her hands firmly around the tail she was holding and gave it a firm yank. Surprised at this action, Vanilla did the same. Tails's pupil's shrunk as he felt his two tails get pulled on by the milf's, a electrifying shock of pleasure surged through his body and he gave a loud scream of pleasure. His cum erupted from the tip of his cock and the rabbit and fox began to lick it all up as it landed on their faces.

"Mm, I have to say Miles" said Rosemary "You have quite a lot of cum stored inside these balls. Mm, and it tastes really nice."

"Heheh, thanks" said Tails.

"Now be a good boy and give Vanilla here a nice hard fuck" said Rosemary, backing off towards the couch, leaving Tails with Vanilla.

"Huh?" said a confused Tails "Don't you want to go first Mom?"

"I would" said Rosemary "But I also wanna see just how you pleasure a lady. Plus, I think I'd rather do the grand finale."

"O...Okay" said Tails, turning his attention to Vanilla "Are you ready?"

"Are you kidding?" asked Vanilla "I've been waiting for a chance to bed you again."

Tails blushed hard as he remembered that unforgettable time he had spent with Vanilla. It was clear that she seemed to have enjoyed the time they spent together just as much, if not even more than he did. He watched as she straddled him, her monstrous breasts swaying and bouncing with each movement she made, her glistening pussy positioned right above his spit and cum coated cock, ready to spear her. Rosemary was watching with interest, ready to see her son in action.

Vanilla's pussy lips kissed the tip of Tails's cock for a brief second, and then Vanilla let the fox feel what they both wanted to feel. She dropped herself onto his cock, screaming out in pleasure as she felt it's size and thickness penetrate her entrance and stretch out her inner walls. Tails growled and moaned as he felt Vanilla tightly wrap around his cock.

Only relishing in the satisfying pleasure of being penetrated by Tails for about five seconds, Vanilla placed her hands firmly on Tails's furry chest and began to lift herself up and down slowly. She groaned in pleasure as she felt his big cock move in and out of her. Tails growled and pulled against his restraints, obviously to no avail as Vanilla squeezed his cock with her vaginal walls. Slowly and surely, Vanilla began to pick up speed. She planted her hands into Tails's chest more firmly and began to ride him like a bull in a rodeo, creating loud smacking sounds each time their hips collided.

Rosemary watched the whole ordeal in front of her. The way Vanilla bounced on her son and the way Tails seemed to be enjoying it showed her that he was quite the stud in bed, even when tied down. The obvious enjoyment and mind numbing pleasure that was written all over Vanilla's face as she rode Tails told her that she was having the time of her life. Obviously being a milf herself, Rosemary had the curves and goods that any man would kill to touch, she was still a little envious of Vanilla considering how much thicker, bustier and curvier than she was. The action in front of her was too hot to not masturbate to, as Rosemary found herself lowering one of her hands to her aching cunt. She moaned as she touched herself, wishing it was her son's big, hard dick slowly inserting itself inside of her.

Tails writhed and wriggled as Vanilla rode him. Her pussy walls were closing in on his shaft with each passing moment, becoming tighter and tighter. As pleasurable as this felt, Tails could not take his eyes off of the tall rabbit bouncing on him, particularly her breasts, her size even unrivalled by Rouge. Watching the two big, fat orbs bounce up and down, with hard erect nipples just begging to be sucked on made Tails drool as he watched the rabbit milf bounce on them, her tits representing basketballs, except squishier. Vanilla didn't miss this, and grinned as he stared hungrily at her.

"See something you want Tails" Vanilla moaned as she continued to ride him.

"AH, Y...Yes" he gasped, half because she thrust down on him particularly hard and half because he had caught her staring.

"Oh don't be so embarrassed" giggled Vanilla "You know what kind of establishment your in."

"R...Right" said Tails, struggling to form a coherent sentence.

"You know" Vanilla said, reaching up to grope her own jiggling tits "If you want to play with these you can just ask nicely and I'll give them to you."

"P...Please?" he asked.

"Mm, please what Tails?" Vanilla moaned teasingly.

"Please... let me suck on your breasts Vanilla" Tails said, blushing in slight embarrassment as he heard his mother give a small chuckle in the background. Nevertheless he was rewarded for his kindness and Vanilla let herself lay down on top of Tails. Because she was so much taller than him, her breasts were smooshed into Tails's face. Tails gasped as he was suddenly buried in the rabbit milf's monstrous tits, but wasted no time in parting his lips and trailing his tongue over one of the large fleshy mounds bigger than his own head.

Vanilla moaned and ran her hands around the back of the fox's head as she felt his mouth and tongue run around the sizeable flesh. She then suddenly clutched at his head as she felt Tails, gently nip her erect nipple. Holding it carefully with his teeth, Tails began to suck on it. She moaned out to him, begging him to keep going and be rougher with her. Eventually Tails released Vanilla's nipple and started to work on the unoccupied one, giving it the same treatment.

As they continued their wild ride, their orgasms drew closer and closer. Rosemary could tell they were getting close because both of them gradually sped up their movements, Vanilla's moans echoing through the room, while Tails's were muffled by the rabbit's bust. The loud smacking sounds they created grew louder and more frequent as they moved faster. Neither of them could take it anymore.

The ropes restraining Tails strained as he felt himself cum. He bucked his hips hard and came deep inside Vanilla, his orgasmic scream could only be heard by the people in the room. Vanilla's scream on the other hand was probably heard by many outside of the room as she felt the satisfaction of cumming herself, and feeling Tails's warm, sticky cum fill her.

"Mm, sooo good" she moaned, as the two of them finished and started to breath to calm down. At least, Vanilla was. She suddenly realised that despite not moving his hips, Tails had not ceased sucking on her breasts. If anything he was still sucking on them hungrily like a newborn child.

"Ah, stop it you naughty boy" she giggled, pulling her chest away from Tails, much to his disappointment.

Vanilla giggled at the fox's pouting and stroked the top of his head affectionately. Tails nuzzled into her hand submissively, making the rabbit smile at him. She slowly lifted herself off of his cock, letting their mixed cum pool onto his cock. Vanilla then turned to Rosemary, who had been masturbating ferociously from watching the show.

"He's all yours Rosemary" said Vanilla, stepping away.

Rosemary nearly jumped to her feet as she walked over to her son, swaying her motherly hips sexually as she approached her son. Here goes nothing.

"Are you ready my son?" she asked him, straddling him.

"Yes, I am" said Tails, his hips quivering to feel his cock enveloped by another set of tight inner folds.

"Tell Mommy what you want" said Rosemary, rubbing her pussy lips up and down his dick teasingly.

"AH, I want you" he cried.

"Hmm? Sorry Miles, I couldn't hear you" giggled Rosemary.

Despite just cumming, and having spent the night with two other pairs of girls, Tails was at a breaking point. Despite the wrongness of fucking his mother, he wasn't doing it to start a relationship with her, he was doing it because he wanted to help her. But there was also how good it would feel. To have Rosemary deny the inevitable at this point was like being denied his favourite food. Fuck it, he wanted to feel the insane pleasure of a females body one more time tonight, and if playing along with Rosemary was going to get him there, he would do it no matter how humiliating it would be. After all, it was just him, his mother and Vanilla who would witness this right?

"Please" he moaned "Fuck me Mommy."

His cheeks burned redder than a tomato and Rosemary smirked widely. She trailed her pussy lips up his cock, until they touched the tip of his cock. It was there when Rosemary slammed her hips down onto his cock. This made her and Tails scream out in blaring pleasure, Rosemary's screams were louder as it had been so long since she took a cock into her pussy, let alone one this big.

"Oooohhhh sooooo gooooood" moaned Rosemary.

"Ohhhhh Mommy" moaned Tails, fidgeting at his mother's tight folds squeezing his length.

Rosemary grinned down foxily at her son, and placed her hands on his shoulders. Her tail was swishing back and forth playfully as she began to slowly lift herself up, and then she dropped herself back on top of him, feeling his cock spear her again. To get used to his size, Rosemary rode him slowly at first, but as she adjusted she began to slowly ride him faster, her son's moans egging her to go faster.

It had been FAR too long since Rosemary last experienced this level of pleasure, and now she was feeling it again. Her son was just as good as Vanilla and the other girls made him out to be. Even when tied down to the bed, he was still able to send electrifying pleasure through her body by thrusting his own hips. It was a little tricky for him to do this, but he managed it and sent his mother into the deep depths of orgasmic ecstasy.

Loud smacking sounds filled the room and Tails and Rosemary's tails waved erratically. Tails growled as his mother's pussy slowly began to get tighter and tighter around his cock, almost like it was trying to milk out his orgasm. Rosemary threw her head back in pleasure as she could feel Tails's cock punch the very end of her tunnel, causing her body to almost collapse in pleasure. But she managed to keep herself steady by gripping Tails's shoulders.

Tails watched his mother, entranced by her sexiness. Of course, she didn't compare to Vanilla, but then again, who actually could. Tails didn't like to compare anyway, he thought his mother was just fine as she was. Wide milfy hips, breasts that were slightly bigger than his own head, topped with rock hard nipples just dying for his attention. He imagined that whenever his mother went out and about, she got a lot of eyes to stare her way. She probably could have gotten herself a new partner whenever she went out. But she wasn't comfortable with going out with a stranger, yet. And he felt somewhat honoured to be trusted by her to satisfy her sexual needs. Even if it was a one-off thing, he was still enjoying himself immensely.

Rosemary could not help but realise that Tails was giving her the same hungry stare he was giving Vanilla earlier. Actually let me rephrase that. Rosemary could not help but realise that Tails was giving her bust the same hungry stare he was giving Vanilla's earlier. She smiled down and him and slowly leaned her chest closer to his face.

"I can tell you want to play with these Miles, so go right ahead" said Rosemary, offering her tits to his face "I'm sorry they aren't as big as Vanilla's but... OH!"

She was cut off as Tails parted his lips and trailed his tongue all around her big right breast, making sure to lick every last square inch of her breast. He then gave the left one the same treatment before going back to the right and closing his lips and teeth around her erect nipple, sucking on it like he used to do as a baby, except no milk was there to quench his thirst, but he didn't need that. He didn't just do this for her pleasure or to fill his own sexual desires, but he also did this to show his mother just how much he loved her. Rosemary found that to be sweet of him and moaned out in pleasure as he sucked on her breasts.

"But you don't seem to mind" she finished "Oooh, that's it baby. Suck on Mommy's titties."

Her fingers raked at the back of his head as she continued to ride him with wild abandon, slowly getting faster and faster. Tails sped up the speed of his own thrusts, nearly matching the speed of his mother's. His arms and legs strained against the rope, trying to be free. But Tails didn't actually care if he was free or not. All he cared about was pulling Rosemary out of the sexual abyss she was trapped in for far too long. Eventually the two of them managed to time their thrusts together perfectly, which cause them both to scream out in orgasmic ecstasy as they edged ever so closer to their inevitable orgasms.

Vanilla watched the show unfold before her. While it was arousing to watch, she was mainly just happy for Rosemary, happy that she was finally going to be satisfied for the first time in years. That being said, she could not help but gently finger herself to this.

"AH. I'M ABOUT TO CUM" Tails cried out, releasing his mothers tits "I'M ABOUT TO CUM MOMMY!"

"Yes Miles" Rosemary cried "Cum for me. CUM FOR MOMMY!"

The two of them were at their breaking point, they couldn't take it anymore. With one final thrust from both of them, mother and son released their cum. Rosemary's juices coated Tails's dick and crotch, and even the bed below them. Tails's own cum rocketed up deep inside of Rosemary, and she sighed in satisfaction of the feeling of being filled after several years. The two of them slowly came down from their orgasmic highs. Rosemary collapsed on top of her son, their tongues flopping out of their mouth's as they tried to get their breath back.

"Wow" said Rosemary "You are as good as Vanilla said you were."

"Heh, thanks Mom" said Tails, as his mother, with some difficulties, lifted herself off of him.

"I'm glad your satisfied now Rosemary" said Vanilla "How do you feel?"

"I feel great" she said "Especially considering my sexual itch has finally calmed down."

"Hey, uh, could you two please untie me now?" asked Tails "I think my arms and legs have had enough of being tied up for one night. Besides, I wanna have a quick cuddle before I leave."

The two milf's smiled sweetly at him and untied him. Tails rubbed his wrists and ankles as he was released, but he was gently laid back on the bed as Vanilla and Rosemary wrapped their arms around him and nuzzled his neck. He returned the affectionate gestures and kissed both women, he then stared deep into the eyes of his Mom.

"Even though this was a one time thing" said Tails "I still enjoyed every second with you Mom."

"So did I" said Rosemary "You wouldn't be too upset if I were to start a relationship with a new partner, would you Miles?"

"Of course not" said Tails, hugging his mother "There's nothing that will stop me from loving you. Heck, I wouldn't mind if you just kept your position here working at the brothel."

"I'll think about it" yawned Rosemary "But I think I need to head home, I'm tuckered out."

"Yeah, me too" said Tails, kissing his mother one last time, and then giving another to Vanilla "Give Rouge my compliments Vanilla."

"With pleasure Tails" said Vanilla, giving him a sexual wink.

After a bit of time hugging the two females, Tails left Vanilla's room and the brothel. He turned back to it and reflected on everything he had done tonight, and he had done it without Sonic, Knuckles and Shadow. He never thought he would have the bravery to come to such a place by himself. Yet, here he was, having accomplished that very thing. He hoped that Rouge would host another night like this again so that Sonic, Shadow and Knuckles could experience the same thing. There was only one thing left on his mind, but he couldn't do it tonight. It involved getting it on with yet another pair of girls, but the rule was three pairs not four, plus he thought he had enough of bondage for one night. He would have to come back tomorrow, and he would have no complaints to come back to this truly amazing place.

With one last look at the building and one last reflection of the good times that he had tonight that would stay in his memory forever, Tails left the brothel with a smile on his face.

"So... he accepted?" Rouge asked Rosemary who was dressed in her blue dress again and back in the brothel owner's office.

"Yes he did" said Rosemary "He was against it at first, but he heard me out and wanted to help me."

"Well I'm glad everything worked out for you Rosemary" said Rouge "Are you sure you don't want to keep working here? I think some of the customers here would kill to be with you."

"I'm flattered" giggled Rosemary "And I will admit, it's a tempting offer. I think I would be more comfortable with handling customers here. And it looks to me that Miles wouldn't mind if I worked here. But I think I will have to say no for now. But, if the offers still on the table, I'd like to take it sometime in the not too distant future."

"Hmmm, you refuse my offer now, but your still drawn back" Rouge smirked "I have no doubt in my mind you'll be back someday. The offer for you to officially join my group of girls will always be on the table Rosemary."

"Thank you" said Rosemary, smiling warmly "Well, maybe I'll see you soon Rouge."

"Sooner than you think" giggled Rouge, feeling like Rosemary would only need half a week of thinking it over before coming back to get a job.

**Notes for the Chapter:**

> ...Or maybe not, considering this story is technically non-canon, and it's up to rdphoenix07 as to whether or not he wants Rosemary to apply for a job at the brothel in 'Rouge's Brothel Reconcile'.
> 
> But anyways, that's a wrap. Before we cap it, I would like to thank SuperSonicBros123 for requesting this idea, and rdphoenix07 for giving me the green light to do it. I really hope you enjoyed this fic, because now it comes to a close... or does it.
> 
> Actually, there is one more thing that this story has to offer. Yep, another chapter is in the works, requested by UltimateCCC. rdphoenix07 has once again, given me the green light to go through with this. However, this chapter will be uploaded as a separate fic, due to SuperSonicBros123 wanting this fic to stay as it is.
> 
> Think of this next chapter as a bonus chapter. Like say, an optional chapter that is only canon to the story if you want it to be. This bonus chapter will be out soon, but as of right now. I do need to focus on getting back into work. And I may need to slow down the production of my stories. So please don't get worried if I upload more scarcely than usual.
> 
> But anyways, that's everything you need to know. Thank you all so much for reading, and I'll see you around.


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